Red Sox: Five players Boston needs to target in Free Agency this winter

3 of 7

BOSTON, MASSACHUSETTS – MARCH 19: A view outside of Fenway Park on March 19, 2020 in Boston, Massachusetts. The NBA, NHL, NCAA and MLB have all announced cancellations or postponements of events because of the COVID-19. (Photo by Maddie Meyer/Getty Images) /

The Boston Red Sox need to be active and aggressive in Free Agency this winter

This season sucked, there’s no way to say it any differently. We all knew that the Red Sox were going to have an uphill battle after trading away Mookie Betts and David Price, while also losing Chris Sale and Eduardo Rodriguez to health issues. But I can’t say that I thought the team would’ve finished in the basement of the AL East and as the fourth-worst team in the entire MLB.

As the dust continues to settle on a massive disappointment of a campaign, it’s incredibly clear that pitching is the Achilles’ heel of this team. The bats weren’t always electric but when they have to dig out of a multi-run hole right out of the gate every night, there’s only so much they can do. Most if not all of the issues this year stemmed from the arms that were trotted out by Boston.

I lost track of how many times I looked at other people in the room and said, “Who the hell is that guy?” AND I COVER THIS TEAM! Looking at the free-agent pool for this winter is like trying to pick the nice piece of fruit out of the pile at the grocery store. Some look good, some could be good, but there are plenty of stinkers around them.

I was able to narrow my list of top free-agent targets down to five though with four of them being pitchers. Are there some weaknesses elsewhere in the Red Sox lineup? Sure, but nothing is in as much need of attention as the pitching staff. With all that said let’s get to the list and see who I think Chaim Bloom should wheel and deal with this offseason.

Cincinnati Reds starting pitcher Trevor Bauer (27) delivers in the first inning of a baseball game against the Milwaukee Brewers, Wednesday, Sept. 23, 2020, at Great American Ball Park in Cincinnati.Milwaukee Brewers At Cincinnati Reds Sept 23 /

SP: Trevor Bauer

This one may get some pushback and I totally understand why. Trevor Bauer is a loudmouth lunatic who has zero filter and that rubs people the wrong way. He has zero disregard for talking smack to batters, umpires, or his favorite target MLB Commissioner Rob Manfred. In my eyes though, that’s a level of venom that this team severely lacked this year. The Red Sox have a guy much like Bauer already on the roster in Sale, but with him not around due to TJS, the team didn’t have that spark.

We don’t know when Sale will return from his TJS and Boston can’t go another season without that person that will kick the team in the ass when they need it. Now that also comes with a worry that the two will butt heads as they serve a similar role in the rotation but it could also ignite a stronger fire in each. You also can’t deny the type of seasons he’s strung together over the last few years, Bauer has been electric.

He really came into his own back in 2018 where he finished 12-6 with a 2.21 ERA, 1.089 WHIP, 221 K, and a league-leading 2.44 FIP all in 175.1 IP. That’s a pretty damn good stat line and one that I wouldn’t hate seeing for the Red Sox. His 2019 was a bit of a mess as he split time between Cleveland and Cincinnati but his 2020 is what has my attention.

In the shortened 2020 season he led the NL in ERA (1.73), ERA + (276), and WHIP (0.795). He led the entire MLB in complete games as well as shutouts at two apiece. Bauer will most likely be named the 2020 NL Cy Young winner and rightfully so, he’s dominated from start to finish this season. His price tag may scare Bloom away but Boston has plenty of money to spend this winter and could feel desperate enough to write the check.

Aug 21, 2020; Kansas City, Missouri, USA; Minnesota Twins starting pitcher Jake Odorizzi (12) pitches against the Kansas City Royals at Kauffman Stadium. Mandatory Credit: Jay Biggerstaff-USA TODAY Sports /

SP: Jake Odorizzi

This one is based on past performance rather than what he’s done lately. We saw a lot of wild things happen during the 2020 season and Jake Odorizzi had quite a few directed his way. First, he strained his back during summer camp and had to miss time. Then when he returned he caught a line drive right to the chest and found himself back on the IL. Lastly, his season ended early as a blister sent him right back to the sidelines and he wasn’t able to return.

So, I’m just going to throw away his 2020 season as the lack of consistency caused his numbers to skyrocket from where he’d been in his previous years. He typically stays within the mid-3.00 to mid-4.00 range as far as his ERA is concerned, barring his rookie season. His best full season to date came last year where he was an All-Star bolstering a 3.51 ERA, 3.36 FIP, 1.208 WHIP with 178 strikeouts through 159 innings.

He’s had some years where those metrics may have been better but this was the first time it seemed like he truly put the puzzle together. As far as where I see him fitting in with this rotation I believe he’d be a strong three or four in the rotation. In my mind Sale, and E-Rod would reclaim their spots at the top with Nathan Eovaldi coming in at a three/four and Martin Perez ending the rotation.

Like Bauer in the previous slide, having Odorizzi on the staff would allow whoever is sitting in the manager’s seat next year to balance things out in a lefty-heavy rotation.

Sep 23, 2020; Cumberland, Georgia, USA; Atlanta Braves relief pitcher Shane Greene (19) pitches against the Miami Marlins during the ninth inning at Truist Park. Mandatory Credit: Dale Zanine-USA TODAY Sports /

RP: Shane Greene

Shane Greene is one hell of a reliever, that’s it, that’s the analysis. We saw over the last two seasons as Boston’s bullpen was worked more and more that there are some serious gaps in the ranks. Even worse, guys who were lights-out last year, looked like they should’ve been in Lowell playing for the Spinners this year. As much as I’ve talked about starting pitchers through this slideshow, I think that relievers will be the most important gets this winter.

Bloom can’t trot out another bullpen staff that was as embarrassing as it was this year. Too many pitchers that didn’t have anything resembling Major League quality stuff absolutely buried the Red Sox. Greene is a guy who not only has great stuff and can come in late in the game but also has close to a decade of service time and won’t be shaken up by a big-game situation.

Let’s look at what he during the regular season, a 2.60 ERA through 27.2 IP in 28 appearances. Last time I checked, those are all good things. He averaged only 6.8 K/9 which isn’t pretty and his H/9 is a scary 7.2, but he did finish with one of his best career WHIP’s at 1.120. So he’s getting the results he just isn’t doing it in a flashy manner by any means. Either way, I’d much rather see him coming out of the bullpen at Fenway Park than some of the jokers from this past year.

September 26, 2020; San Francisco, California, USA; San Diego Padres relief pitcher Trevor Rosenthal (47) pitches against the San Francisco Giants during the ninth inning at Oracle Park. Mandatory Credit: Kyle Terada-USA TODAY Sports /

RP: Trevor Rosenthal

My second Trevor of the day is Trevor Rosenthal. This pick felt like a no-brainer for me as once again, he’s a veteran reliever with big-game experience that can boost this Red Sox bullpen. Rosenthal has close to a decade of service time in the Majors and in those nearly ten years he’s pitched in the postseason in five of them. I can’t argue against a dude that has made it to the playoffs in five of his eight career years in the bigs.

For all of the success he’s had there is a downside as he has undergone Tommy John which caused him to miss out on the 2018 season. Before he needed the surgery though his numbers were electric and he was a shutdown closer. In his return in 2019, however, there was clearly some rust on the right arm as he finished with 13.50 ERA split across time with Washington and Detroit. Similar to a few of the names I’ve already mentioned, 2020 is what I care about the most.

Rosenthal started the season with Kansas City and made his way to the San Diego Padres at the trade deadline. Over the course of the year, he finished with a 1.90 ERA, 11 saves, 13.8 K/9, and a stunning 0.845 WHIP through 23.2 IP. If Bloom and the Red Sox were to spend heavily on anyone this winter, I wouldn’t hate it being Rosenthal. He’s shown that he can be a reliable closer not only before TJS but after as well.

The Red Sox have struggled greatly to close out games late since the departure of Craig Kimbrel after 2018, with Brandon Workman emerging in 2019. However, Workman was dealt at the deadline and Boston doesn’t have a real option to replace him. Bringing Rosenthal to the Sox would be a strong move for Chaim and could cross a serious need off of the shopping list this winter.

BOSTON, MA – APRIL 12: Jackie Bradley Jr. #19 of the Boston Red Sox makes a leaping catch in the eighth inning agains the Baltimore Orioles at Fenway Park on April 12, 2019 in Boston, Massachusetts. (Photo by Kathryn Riley /Getty Images) /

CF: Jackie Bradley Jr

This one should be clear and obvious to anyone that watches this team. Are there some options out on the market this winter? Better believe it. Are they all the quality of Jackie Bradley Jr? Absolutely not. Many fans will be chirping that the Red Sox should go out and get Geroge Springer, but I can’t agree with that sentiment. Springer is far and above the better hitter but nobody can patrol Fenway Park like JBJ. Plus the price tag for Springer will be ASTROnomical, see what I did there?

Bringing back Jackie instead of splashing a ton of cash for Springer is the right play here for the Red Sox. Not only is a familiar with Fenway, but he’s been a stalwart in the organization since his promotion in 2013, despite the team’s best efforts to ship him off. We saw Jackie hit the ball this year like he hasn’t done in some time, or possibly even ever. Add in the fact that he posted another Gold Glove caliber year in center, and he’d be a great addition for any team.

Boston has a great prospect in Jarren Duran seemingly chomping at the bit to get to the Majors but I’m not sure if he’s Opening Day ready. Earlier this year, I pegged Duran as the heir apparent to JBJ and I still believe that, but I’d like for him to have a year with Jackie to learn the ropes. It would also give Jackie a chance to leave Boston on a better note as the team is poised to be far more competitive in 2021.

If I’m Chaim Bloom, I set aside a majority of my budget to fix the pitching but leave enough to offer JBJ a respectable deal that he can sleep at night accepting. He was set to make $11M this year before the pandemic mangled the salary system, so I would stay in that realm for 2021. Something along the lines of 2 years/$24M would be perfect. Boston has the space thanks to resettign the CBT threshold and it’ll give the veteran a raise.

BOSTON, MA – MAY 04: The Boston Red Sox 2018 World Series Trophy is seen at the Boston Arts Academy Foundation’s annual BAA Honors Gala at InterContinental Boston on May 4, 2019 in Boston, Massachusetts. In October 2018 Boston Arts Academy is the city’s only public high school for visual and performing arts and broke ground on a new $125 million facility scheduled to open in 2021. (Photo by Paul Marotta/Getty Images) /

What’s on the horizon for the Red Sox?

So, what’s next Red Sox Nation? I honestly don’t know and I don’t think the team does either. There’s an air of optimism as we’ve recently gotten good news about both Chris Sale and Eduardo Rodriguez. There was also the emergence of numerous young players that stepped up big and showed they can hang at this level. But the big decider for 2021 all lies in free agency this winter.